Behind The Music | ‘Dirty Diana’ by Michael Jackson

the detail.
8 min readSep 19, 2021

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‘Dirty Diana’. While some Michael Jackson’s songs had hidden meanings, the lyrics to this track are explicit and left little room for interpretation. Much like Thriller’s ‘Beat It’, the dark and sordid musical creation presents a harder rock sound, but with a lyrical content similar to that of ‘Billie Jean’, delving into the artists own internal struggle as he attempts to resist a lecherous groupie with dangerous intentions.

After topping the Billboard charts in 1988, Michael Jackson’s final single from his ‘Bad’ album to do so, Jackson became the first artist ever with five no. 1 hits from a single album. Continuing Michael Jackson’s ground-breaking run off success both commercially and artistically as the true King of Pop.

This is the story behind the inspiration, production and commercial reaction to one of pop history’s most iconic music releases. Michael Jackson’s 1988 hit, ‘Dirty Diana’.

After the meteoric success of Thriller, Michael Jackson identified certain conventions that proved popular which he now wanted to further expand on for his next record. One of them being his success in genre-blending with the track ‘Beat It’, allowing him to crossover into the mainstream by dabbling in the heavy metal and rock genre. He saw this theory further substantiated, with the artistic victories of his somewhat rival, Prince. With the release of 1984’s ‘Purple Rain’, a record which combined multiple layers of guitars, keyboards, synthesizers, drum machines and psychedelic rock, Michael Jackson saw the radical endeavour garner Prince both the critical and commercial success he so craved.

Most notably Prince’s ‘Darling Nikki’, a track that tells the story of a ‘sex fiend’ who seduces the singer, which compared with the slick production of the other songs on the album was deliberately engineered to have a raw and live feel. The song gained wide notoriety for its explicit lyrics and references to female masturbation and was responsible for the creation of the infamous parental advisory sticker.

The track’s production and controversial subject matter intrigued Michael Jackson, who felt that if he was able to create his own ‘Darling Nikki’, Jackson could spice up his image with an element of danger and counteract growing criticism for being overly produced, as well as having a sanitised ‘good guy’ image. Much like with his artistic triumph, ‘Billie Jean’, Michael took inspiration from the women on the side-lines with deep desires of fortune and notoriety. After decades of stardom, Michael Jackson certainly had his fair share of first-hand experiences to draw from. He later explained, ‘the song is about certain kind of girls that hang around concerts or clubs, you know, they call them groupies. I’ve lived with that all my life. These girls they do everything with the band, you know, everything you could imagine’.

Much like Prince’s ‘Darling Nikki’, Michael Jackson tells the tale of ‘Dirty Diana’. Diana is depicted as somewhat of a professional groupie, who knows when popular musicians are coming to town and how to get close to them. One way she attempts to entice Michael is by promising to fulfil any and every bedroom fantasy he may have. Even though the singer continuously refuses her sensual advances, she refuses to let up. In fact, he tells Diana that his preoccupation is to get back to his woman as opposed to hooking up with her. Experienced in her craft and being the persistent temptress that she is, her mission is to foil this plan at all costs and the song’s ending makes it unclear whether she is successful in doing so.

In an interview for the special edition release of the Bad album, Jackson’s producer Quincy Jones said this song was ‘in the spirit of ‘Killing Me Softly With His Song’. He also said that Jackson’s flair for drama comes into play in this track, as he was a very theatrical songwriter and performer.

Recorded in 1986, the track required an authentic hard rock edge, which required some serious guitar shredding. Eddie Van Halen was enlisted to play on Jackson’s previous guitar-heavy hit, ‘Beat It’, but his producer Quincy Jones needed someone else for this one. Van Halen’s producer Ted Templeman was working for Warner Brothers Records, which had recently signed Billy Idol’s guitarist Steve Stevens to a solo deal, so Templeman suggested him to Jones. It was Templeman who also suggested Eddie Van Halen for ‘Beat It’.

When Stevens got the call from Quincy Jones, it took him a while to believe it was really him, but he was thrilled to get the opportunity. When he played on the track, Stevens was pleasantly surprised. ‘The song is a lot darker and heavier than I thought I would be playing on, with an underlining current of nastiness to it,’ he said. ‘It was great for me — I was really glad it wasn’t like a pop song — it was dark, and it allowed me to dig into the heavier side of what I do.’

Overall, Stevens recounts that he had a great experience working with Jackson, ‘Michael was very musical. He understood what I was about and was trying to get the best out of my performance’.

The song’s five-minute music video was directed by Joe Pytka, who had previously directed the Bad album’s ‘The Way You Make Me Feel’. Filmed during March 1988, the video mostly consisted of a staged performance which was shot in Long Beach, Los Angeles. Guitarist Steve Stevens was also featured onstage during the performance as well.

The actress in the video who played Dirty Diana was Lisa Dean. The 5-foot 9 model from San Diego, California, was chosen out of hundreds of girls who auditioned for the role. Having previously modelled for Vogue Magazine as well as appeared in the music video for ‘Round and Round’ by 80s heavy metal band, Ratt, Dean was chosen for the most part due to her admirable legs. ‘My agent said they were looking for what Michael Jackson thought would be every man’s fantasy woman… Dirty Diana had to be the baddest, sexiest, bitchiest, most elegant and drop-dead beautiful woman ever seen on the screen’.

At first, Lisa Dean wasn’t sure she could fulfil such a high order, but gave it her best shot. Squeezing into the tightest, shortest skirt possible — less than 12 inches, she wore no stocking and teetered in high, high heels. ‘When I first saw the finished video, even I was astonished at how sexy I looked… after being narrowed down to the last 15 girls, I was the first video played to Michael and he immediately said ‘that’s it, she’s the one. I want her — she is Dirty Diana.’

Although Michael Jackson was immediately enamoured by Dean’s legs, this didn’t mean that he was romantically interested in her. As based on her own account Michael didn’t flirt much and spent most of his downtime during the video shoot chilling with his pet chimp, Bubbles. ‘He is a magical, sweet and generous person’ she recounted.

The only complaints Lisa Dean had about the job was her restrictive outfit and the standard $300 day-rate she got paid on the two-week shoot. ‘At first, I was so upset that all people were seeing was my legs… that was very disappointing. But the video director told me it was better to keep the mystery of the face behind the legs, and let people wonder.’

Released on April 18th, 1988, ‘Dirty Diana’ peaked at no. 1 on the Billboard Hot 100 on July 2nd, making Jackson the first artist ever with five no. 1 hits from one album. The previous four being ‘I Just Can’t Stop Loving You’, ‘Bad’, ‘The Way You Make Me Feel’, and ‘Man in The Mirror’.

Although commercially a triumph, ‘Dirty Diana’ received mixed reviews. Music critic, Stephen Thomas Erlewine, shockingly wrote that ‘Dirty Diana’ as well as ‘Man in the Mirror’ were ‘showcasing Jackson at his worst’. Robert Christgau viewed ‘Dirty Diana’ as deeply ‘misogynistic’ and Jon Pareles, a writer for The New York Times, described ‘Dirty Diana’ as reducing Jackson to a ‘terrified whimper’. While John Tatlock considered ‘Dirty Diana’ as a ‘confused lumbering slog of a song,’ thinking that ‘Jackson was never convincing in this kind of role, a boy-child trying to write a song about the kind of woman he never meets in the kind of places he’s certainly never been to.’ Although the video won the ‘Number-One Video in the World’ at the second World Music Awards held on April 14, 1989.

At the time of its release, there were persistent rumours that the “Diana” in question was in fact referencing Jackson’s close friend, Diana Ross, who he reportedly had a persistent crush on for many years and the song was a jab against the Supremes star after recently getting married. However, Michael himself has asserted that this song was indeed about a random admirer, not one of his peers. Miss Ross later embraced the rumours and started using the song as an overture at her concerts shortly before appearing on stage.

‘Dirty Diana’ was performed during the second leg of Michael Jackson’s Bad World Tour. According to Jackson in an interview with Barbara Walters, ‘Dirty Diana’ was scheduled for a live 1988 performance at London’s Wembley Stadium; however, Jackson felt the song would be an insult to Diana, Princess of Wales, who was in attendance, so he had it removed. When Jackson met Princess Diana herself before the concert in question, he recounted ‘I took it out of the show in honour of her royal highness. She took me away and she said, are you going to do ‘Dirty Diana’? So, I said, ‘No I took it out of the show because of you.’ She said, ‘No! I want you to do it. Do the song. And she told me it was an honour to meet me. And I said, ‘It’s an honour to meet you.’ After Diana informed Jackson that the song was actually one of her personal favourites, Jackson re-added the song to the set-list and performed it for her majesty and a sea of thousands.

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the detail.

Cut through the headlines and understand the man, the music and the magic behind Michael Jackson.